(1S,5R,7R,30S)-14-De-oxy-isogarcinol.

The title compound, C(38)H(50)O(5) {systematic name: 10-(3-hy-droxy-benzo-yl)-2,2,7,7-tetra-methyl-3,6,8-tris-(3-methyl-but-2-en-yl)-3,4,4a,5,6,7-hexa-hydro-4a,8-methano-2H-cyclo-octa-[b]pyran-9,11(8H)-dione}, is a polyisoprenylated benzophenone, isolated for the first time from the fruits of Garcinia indica during our investigation of bioactive compounds from this plant and their large-scale extraction. The relative configuration of the title compound was chosen based on comparison of its spectroscopic and optical rotation data with that of the isomorphous and isostructural compound isogarcinol, whose absolute configuration is known. The crystal packing features O-H⋯O hydrogen bonds. A Cambridge Structural Database analysis revealed that the crystal structure reported here is isomorphous and isostructural with that of isogarcinol.

Related literature

For background information on the plant Garcinia indica and its biologically active compounds, see: Anonymous (1956 ▶); Padhye et al. (2009 ▶); Jayaprakasha & Sakariah (2002 ▶); Yamaguchi et al. (2000a ▶,b ▶); Sang et al. (2001 ▶). For related compounds, see: Krishnamurthy et al. (1981 ▶, 1982 ▶); Rao et al. (1980a ▶,b ▶); Sahu et al. (1989 ▶); Marti et al. (2009 ▶). For the isolation, purification and spectroscopic study of the title compound, see: Kaur et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the determination of absolute configuration, see: Flack (1983 ▶); Hooft et al. (2008 ▶).

Experimental

Crystal data

C38H50O5

M = 586.78

Orthorhombic,

a = 11.561 (5) Å

b = 14.657 (7) Å

c = 20.457 (10) Å

V = 3466 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.38 × 0.24 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

22425 measured reflections

4711 independent reflections

2083 reflections with I > 2σ(I)

R int = 0.119

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.246

S = 0.96

4711 reflections

395 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶)and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020788/nr2023sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020788/nr2023Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020788/nr2023Isup4.cdx

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H50O5	Dx = 1.124 Mg m−3
Mr = 586.78	Melting point: 508.15 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 11.561 (5) Å	Cell parameters from 1674 reflections
b = 14.657 (7) Å	θ = 2.5–18.3°
c = 20.457 (10) Å	µ = 0.07 mm−1
V = 3466 (3) Å3	T = 293 K
Z = 4	Rectangular, colourless'
F(000) = 1272	0.38 × 0.24 × 0.14 mm

Bruker SMART APEX CCD diffractometer	2083 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.119
Graphite monochromator	θmax = 28.4°, θmin = 2.0°
phi and ω scans	h = −7→15
22425 measured reflections	k = −19→19
4711 independent reflections	l = −26→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.1315P)2] where P = (Fo2 + 2Fc2)/3
4711 reflections	(Δ/σ)max = 0.014
395 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	−0.0105 (3)	0.0536 (3)	0.5068 (2)	0.0845 (11)
O2	0.3125 (3)	−0.0825 (2)	0.42986 (16)	0.0701 (10)
O3	0.2529 (3)	−0.0440 (3)	0.65177 (17)	0.0787 (11)
O4	0.4668 (3)	−0.1232 (3)	0.5609 (2)	0.0835 (11)
O5	0.4003 (4)	0.2725 (3)	0.5150 (4)	0.135 (2)
H5	0.4376	0.3191	0.5220	0.203*
C1	0.1090 (4)	−0.0679 (3)	0.4651 (2)	0.0612 (13)
C2	0.2389 (4)	−0.0657 (3)	0.4788 (2)	0.0553 (11)
C3	0.2840 (4)	−0.0539 (3)	0.5391 (2)	0.0575 (12)
C4	0.2107 (4)	−0.0478 (3)	0.5971 (2)	0.0601 (12)
C5	0.0773 (4)	−0.0422 (3)	0.5880 (2)	0.0605 (12)
C6	0.0215 (5)	−0.1426 (3)	0.5949 (3)	0.0678 (14)
C7	0.0697 (5)	−0.2085 (3)	0.5419 (2)	0.0696 (14)
H7	0.0158	−0.2601	0.5416	0.083*
C8	0.0611 (5)	−0.1671 (3)	0.4724 (3)	0.0708 (14)
H8A	−0.0195	−0.1673	0.4592	0.085*
H8B	0.1027	−0.2064	0.4424	0.085*
C9	0.0525 (4)	−0.0111 (3)	0.5182 (3)	0.0625 (13)
C10	0.4138 (5)	−0.0532 (4)	0.5494 (2)	0.0622 (13)
C11	0.4724 (4)	0.0363 (4)	0.5432 (2)	0.0628 (12)
C12	0.4122 (5)	0.1149 (4)	0.5326 (3)	0.0725 (14)
H12	0.3319	0.1126	0.5297	0.087*
C13	0.4684 (5)	0.1984 (4)	0.5258 (3)	0.0869 (18)
C14	0.5866 (6)	0.2017 (5)	0.5292 (3)	0.0953 (19)
H14	0.6249	0.2569	0.5234	0.114*
C15	0.6485 (6)	0.1240 (6)	0.5410 (4)	0.104 (2)
H15	0.7287	0.1274	0.5444	0.125*
C16	0.5940 (5)	0.0400 (5)	0.5482 (3)	0.0858 (17)
H16	0.6368	−0.0126	0.5560	0.103*
C17	0.0284 (5)	0.0262 (4)	0.6383 (3)	0.0789 (16)
H17A	−0.0537	0.0337	0.6303	0.095*
H17B	0.0370	0.0004	0.6817	0.095*
C18	0.0844 (5)	0.1186 (4)	0.6376 (3)	0.0802 (16)
H18	0.1627	0.1207	0.6272	0.096*
C19	0.0332 (6)	0.1967 (4)	0.6502 (3)	0.0833 (17)
C20	0.1027 (7)	0.2848 (4)	0.6480 (4)	0.110 (2)
H20A	0.1775	0.2730	0.6295	0.164*
H20B	0.1118	0.3082	0.6916	0.164*
H20C	0.0628	0.3289	0.6217	0.164*
C21	−0.0933 (7)	0.2062 (5)	0.6651 (5)	0.139 (3)
H21A	−0.1315	0.1490	0.6574	0.209*
H21B	−0.1264	0.2522	0.6374	0.209*
H21C	−0.1030	0.2235	0.7100	0.209*
C22	−0.1116 (5)	−0.1336 (4)	0.5847 (3)	0.0889 (18)
H22A	−0.1268	−0.1093	0.5420	0.133*
H22B	−0.1431	−0.0933	0.6172	0.133*
H22C	−0.1470	−0.1925	0.5887	0.133*
C23	0.0426 (6)	−0.1819 (4)	0.6630 (3)	0.0832 (18)
H23A	0.1243	−0.1880	0.6703	0.125*
H23B	0.0066	−0.2407	0.6663	0.125*
H23C	0.0103	−0.1418	0.6953	0.125*
C24	0.1921 (6)	−0.2525 (3)	0.5560 (3)	0.0761 (15)
H24A	0.2375	−0.2511	0.5161	0.091*
H24B	0.2320	−0.2156	0.5883	0.091*
C25	0.1862 (6)	−0.3480 (4)	0.5799 (3)	0.0906 (19)
H25	0.1379	−0.3873	0.5569	0.109*
C26	0.2426 (5)	−0.3839 (4)	0.6309 (3)	0.0896 (18)
C27	0.2321 (7)	−0.4839 (5)	0.6458 (5)	0.158 (4)
H27A	0.1819	−0.5121	0.6144	0.238*
H27B	0.2005	−0.4918	0.6889	0.238*
H27C	0.3071	−0.5118	0.6437	0.238*
C28	0.3171 (6)	−0.3303 (6)	0.6760 (4)	0.114 (2)
H28A	0.3038	−0.2663	0.6693	0.171*
H28B	0.3969	−0.3440	0.6675	0.171*
H28C	0.2988	−0.3458	0.7204	0.171*
C29	0.0846 (5)	−0.0309 (4)	0.3958 (3)	0.0804 (16)
H29A	0.0650	−0.0814	0.3672	0.097*
H29B	0.0184	0.0098	0.3975	0.097*
C30	0.1879 (5)	0.0203 (4)	0.3673 (2)	0.0715 (14)
H30	0.2072	0.0694	0.3979	0.086*
C31	0.2921 (5)	−0.0422 (4)	0.3634 (2)	0.0687 (14)
C32	0.4033 (6)	0.0073 (5)	0.3505 (3)	0.106 (2)
H32A	0.4656	−0.0358	0.3479	0.160*
H32B	0.4181	0.0496	0.3853	0.160*
H32C	0.3974	0.0400	0.3099	0.160*
C33	0.2774 (7)	−0.1222 (5)	0.3173 (3)	0.112 (3)
H33A	0.2059	−0.1528	0.3267	0.169*
H33B	0.3406	−0.1640	0.3229	0.169*
H33C	0.2764	−0.1005	0.2730	0.169*
C34	0.1564 (6)	0.0651 (5)	0.3022 (3)	0.097 (2)
H34A	0.2268	0.0814	0.2791	0.116*
H34B	0.1145	0.0216	0.2754	0.116*
C35	0.0839 (7)	0.1488 (6)	0.3112 (3)	0.115 (3)
H35	0.1070	0.1871	0.3451	0.138*
C36	−0.0068 (8)	0.1762 (9)	0.2788 (4)	0.148 (4)
C37	−0.0607 (10)	0.2708 (9)	0.2936 (6)	0.228 (7)
H37A	−0.0223	0.2976	0.3306	0.342*
H37B	−0.1415	0.2637	0.3032	0.342*
H37C	−0.0516	0.3098	0.2563	0.342*
C38	−0.0624 (9)	0.1254 (12)	0.2261 (5)	0.227 (7)
H38A	−0.0495	0.0613	0.2323	0.340*
H38B	−0.0304	0.1440	0.1849	0.340*
H38C	−0.1440	0.1376	0.2265	0.340*

	U11	U22	U33	U12	U13	U23
O1	0.087 (3)	0.066 (2)	0.101 (3)	0.012 (2)	−0.018 (2)	0.011 (2)
O2	0.069 (2)	0.078 (2)	0.063 (2)	−0.0018 (19)	−0.0079 (18)	0.0034 (18)
O3	0.085 (3)	0.091 (3)	0.060 (2)	−0.003 (2)	−0.0164 (19)	−0.0014 (19)
O4	0.074 (3)	0.070 (2)	0.107 (3)	0.013 (2)	−0.021 (2)	0.003 (2)
O5	0.100 (4)	0.067 (3)	0.239 (7)	−0.021 (3)	−0.020 (4)	0.030 (4)
C1	0.057 (3)	0.064 (3)	0.062 (3)	−0.012 (2)	−0.007 (2)	0.007 (3)
C2	0.057 (3)	0.049 (3)	0.060 (3)	−0.005 (2)	−0.006 (2)	0.005 (2)
C3	0.062 (3)	0.047 (2)	0.064 (3)	−0.007 (2)	−0.009 (2)	0.006 (2)
C4	0.068 (3)	0.048 (3)	0.064 (3)	−0.007 (2)	−0.012 (3)	0.002 (2)
C5	0.067 (3)	0.050 (2)	0.065 (3)	−0.007 (2)	0.001 (2)	0.002 (2)
C6	0.061 (3)	0.061 (3)	0.081 (4)	−0.013 (2)	0.003 (3)	0.009 (3)
C7	0.078 (4)	0.052 (3)	0.079 (3)	−0.022 (3)	−0.009 (3)	0.003 (3)
C8	0.071 (3)	0.065 (3)	0.076 (3)	−0.020 (3)	−0.012 (3)	−0.001 (3)
C9	0.059 (3)	0.051 (3)	0.078 (3)	−0.012 (2)	−0.010 (3)	0.008 (2)
C10	0.061 (3)	0.064 (3)	0.063 (3)	0.003 (3)	−0.014 (2)	−0.005 (2)
C11	0.055 (3)	0.065 (3)	0.068 (3)	−0.001 (3)	−0.013 (2)	0.000 (3)
C12	0.053 (3)	0.067 (3)	0.097 (4)	−0.013 (3)	−0.012 (3)	0.002 (3)
C13	0.072 (4)	0.067 (4)	0.122 (5)	−0.021 (3)	−0.016 (4)	0.011 (4)
C14	0.081 (5)	0.084 (4)	0.121 (5)	−0.036 (4)	−0.004 (4)	0.007 (4)
C15	0.058 (4)	0.122 (6)	0.132 (6)	−0.026 (4)	−0.007 (4)	−0.010 (5)
C16	0.063 (4)	0.094 (4)	0.100 (4)	−0.008 (3)	−0.011 (3)	−0.006 (4)
C17	0.080 (4)	0.071 (3)	0.086 (4)	0.005 (3)	0.011 (3)	−0.001 (3)
C18	0.073 (4)	0.063 (3)	0.104 (4)	0.000 (3)	−0.002 (3)	−0.015 (3)
C19	0.092 (5)	0.073 (4)	0.085 (4)	0.004 (3)	−0.001 (3)	−0.014 (3)
C20	0.130 (6)	0.068 (4)	0.131 (6)	−0.007 (4)	0.005 (5)	−0.024 (4)
C21	0.101 (6)	0.109 (5)	0.209 (9)	0.009 (5)	0.045 (6)	−0.063 (6)
C22	0.070 (4)	0.083 (4)	0.114 (5)	−0.023 (3)	0.002 (3)	0.014 (4)
C23	0.104 (5)	0.071 (4)	0.075 (4)	−0.012 (3)	0.004 (3)	0.019 (3)
C24	0.092 (4)	0.049 (3)	0.087 (4)	0.005 (3)	0.006 (3)	0.008 (3)
C25	0.102 (5)	0.052 (3)	0.117 (5)	−0.013 (3)	−0.009 (4)	0.001 (3)
C26	0.076 (4)	0.087 (4)	0.106 (5)	0.013 (4)	0.006 (4)	0.023 (4)
C27	0.101 (6)	0.105 (6)	0.268 (12)	0.010 (5)	0.000 (6)	0.101 (7)
C28	0.083 (5)	0.155 (7)	0.104 (5)	0.037 (5)	−0.009 (4)	−0.002 (5)
C29	0.073 (4)	0.098 (4)	0.070 (3)	−0.006 (3)	−0.021 (3)	0.007 (3)
C30	0.081 (4)	0.076 (3)	0.057 (3)	−0.005 (3)	−0.006 (3)	0.008 (3)
C31	0.076 (4)	0.073 (3)	0.058 (3)	0.001 (3)	−0.004 (2)	0.000 (3)
C32	0.098 (5)	0.131 (6)	0.089 (4)	−0.014 (5)	0.014 (4)	0.019 (4)
C33	0.142 (7)	0.106 (5)	0.089 (4)	0.026 (5)	−0.028 (4)	−0.031 (4)
C34	0.108 (5)	0.110 (5)	0.072 (4)	0.004 (4)	−0.007 (3)	0.019 (3)
C35	0.122 (6)	0.141 (6)	0.083 (4)	0.032 (5)	−0.007 (4)	0.035 (4)
C36	0.114 (6)	0.238 (11)	0.092 (6)	0.032 (7)	0.018 (5)	0.074 (7)
C37	0.211 (12)	0.315 (17)	0.158 (9)	0.171 (13)	0.044 (8)	0.097 (10)
C38	0.115 (8)	0.43 (2)	0.132 (8)	−0.039 (12)	−0.033 (7)	0.045 (12)

O1—C9	1.219 (6)	C21—H21B	0.9600
O2—C2	1.337 (6)	C21—H21C	0.9600
O2—C31	1.500 (6)	C22—H22A	0.9600
O3—C4	1.221 (5)	C22—H22B	0.9600
O4—C10	1.218 (6)	C22—H22C	0.9600
O5—C13	1.359 (8)	C23—H23A	0.9600
O5—H5	0.8200	C23—H23B	0.9600
C1—C9	1.517 (7)	C23—H23C	0.9600
C1—C2	1.527 (7)	C24—C25	1.485 (7)
C1—C29	1.544 (7)	C24—H24A	0.9700
C1—C8	1.563 (7)	C24—H24B	0.9700
C2—C3	1.352 (6)	C25—C26	1.338 (9)
C3—C4	1.460 (7)	C25—H25	0.9300
C3—C10	1.515 (7)	C26—C28	1.487 (10)
C4—C5	1.556 (7)	C26—C27	1.503 (10)
C5—C9	1.526 (7)	C27—H27A	0.9600
C5—C17	1.544 (7)	C27—H27B	0.9600
C5—C6	1.612 (7)	C27—H27C	0.9600
C6—C23	1.528 (7)	C28—H28A	0.9600
C6—C7	1.556 (7)	C28—H28B	0.9600
C6—C22	1.558 (8)	C28—H28C	0.9600
C7—C8	1.549 (7)	C29—C30	1.527 (8)
C7—C24	1.581 (8)	C29—H29A	0.9700
C7—H7	0.9800	C29—H29B	0.9700
C8—H8A	0.9700	C30—C31	1.516 (8)
C8—H8B	0.9700	C30—C34	1.529 (8)
C10—C11	1.482 (7)	C30—H30	0.9800
C11—C12	1.363 (7)	C31—C32	1.499 (9)
C11—C16	1.411 (8)	C31—C33	1.515 (8)
C12—C13	1.393 (7)	C32—H32A	0.9600
C12—H12	0.9300	C32—H32B	0.9600
C13—C14	1.370 (9)	C32—H32C	0.9600
C14—C15	1.366 (9)	C33—H33A	0.9600
C14—H14	0.9300	C33—H33B	0.9600
C15—C16	1.391 (9)	C33—H33C	0.9600
C15—H15	0.9300	C34—C35	1.498 (10)
C16—H16	0.9300	C34—H34A	0.9700
C17—C18	1.500 (8)	C34—H34B	0.9700
C17—H17A	0.9700	C35—C36	1.304 (11)
C17—H17B	0.9700	C35—H35	0.9300
C18—C19	1.314 (8)	C36—C38	1.459 (15)
C18—H18	0.9300	C36—C37	1.551 (15)
C19—C21	1.501 (10)	C37—H37A	0.9600
C19—C20	1.522 (9)	C37—H37B	0.9600
C20—H20A	0.9600	C37—H37C	0.9600
C20—H20B	0.9600	C38—H38A	0.9600
C20—H20C	0.9600	C38—H38B	0.9600
C21—H21A	0.9600	C38—H38C	0.9600
C2—O2—C31	120.3 (4)	C6—C22—H22B	109.5
C13—O5—H5	109.5	H22A—C22—H22B	109.5
C9—C1—C2	106.3 (4)	C6—C22—H22C	109.5
C9—C1—C29	112.7 (4)	H22A—C22—H22C	109.5
C2—C1—C29	109.9 (4)	H22B—C22—H22C	109.5
C9—C1—C8	106.8 (4)	C6—C23—H23A	109.5
C2—C1—C8	110.5 (4)	C6—C23—H23B	109.5
C29—C1—C8	110.5 (4)	H23A—C23—H23B	109.5
O2—C2—C3	117.5 (4)	C6—C23—H23C	109.5
O2—C2—C1	119.1 (4)	H23A—C23—H23C	109.5
C3—C2—C1	123.3 (4)	H23B—C23—H23C	109.5
C2—C3—C4	121.7 (4)	C25—C24—C7	113.8 (5)
C2—C3—C10	120.6 (4)	C25—C24—H24A	108.8
C4—C3—C10	117.5 (4)	C7—C24—H24A	108.8
O3—C4—C3	121.0 (5)	C25—C24—H24B	108.8
O3—C4—C5	120.2 (5)	C7—C24—H24B	108.8
C3—C4—C5	118.8 (4)	H24A—C24—H24B	107.7
C9—C5—C17	111.1 (4)	C26—C25—C24	127.2 (6)
C9—C5—C4	108.3 (4)	C26—C25—H25	116.4
C17—C5—C4	108.5 (4)	C24—C25—H25	116.4
C9—C5—C6	106.2 (4)	C25—C26—C28	124.0 (6)
C17—C5—C6	112.8 (4)	C25—C26—C27	120.1 (7)
C4—C5—C6	109.8 (4)	C28—C26—C27	115.9 (7)
C23—C6—C7	110.1 (4)	C26—C27—H27A	109.5
C23—C6—C22	108.2 (5)	C26—C27—H27B	109.5
C7—C6—C22	108.3 (5)	H27A—C27—H27B	109.5
C23—C6—C5	111.1 (4)	C26—C27—H27C	109.5
C7—C6—C5	111.3 (4)	H27A—C27—H27C	109.5
C22—C6—C5	107.8 (5)	H27B—C27—H27C	109.5
C8—C7—C6	111.9 (4)	C26—C28—H28A	109.5
C8—C7—C24	112.6 (4)	C26—C28—H28B	109.5
C6—C7—C24	116.6 (4)	H28A—C28—H28B	109.5
C8—C7—H7	104.8	C26—C28—H28C	109.5
C6—C7—H7	104.8	H28A—C28—H28C	109.5
C24—C7—H7	104.8	H28B—C28—H28C	109.5
C7—C8—C1	115.4 (4)	C30—C29—C1	112.3 (4)
C7—C8—H8A	108.4	C30—C29—H29A	109.1
C1—C8—H8A	108.4	C1—C29—H29A	109.1
C7—C8—H8B	108.4	C30—C29—H29B	109.1
C1—C8—H8B	108.4	C1—C29—H29B	109.1
H8A—C8—H8B	107.5	H29A—C29—H29B	107.9
O1—C9—C1	123.1 (5)	C31—C30—C29	110.2 (5)
O1—C9—C5	121.7 (5)	C31—C30—C34	113.8 (5)
C1—C9—C5	115.2 (4)	C29—C30—C34	111.0 (5)
O4—C10—C11	122.2 (5)	C31—C30—H30	107.2
O4—C10—C3	121.2 (5)	C29—C30—H30	107.2
C11—C10—C3	116.5 (4)	C34—C30—H30	107.2
C12—C11—C16	119.2 (5)	O2—C31—C32	102.5 (4)
C12—C11—C10	121.9 (4)	O2—C31—C30	108.4 (4)
C16—C11—C10	118.9 (5)	C32—C31—C30	113.4 (5)
C11—C12—C13	121.3 (5)	O2—C31—C33	106.1 (5)
C11—C12—H12	119.3	C32—C31—C33	111.1 (5)
C13—C12—H12	119.3	C30—C31—C33	114.3 (5)
O5—C13—C14	123.9 (6)	C31—C32—H32A	109.5
O5—C13—C12	116.7 (5)	C31—C32—H32B	109.5
C14—C13—C12	119.4 (6)	H32A—C32—H32B	109.5
C15—C14—C13	120.2 (6)	C31—C32—H32C	109.5
C15—C14—H14	119.9	H32A—C32—H32C	109.5
C13—C14—H14	119.9	H32B—C32—H32C	109.5
C14—C15—C16	121.3 (6)	C31—C33—H33A	109.5
C14—C15—H15	119.4	C31—C33—H33B	109.5
C16—C15—H15	119.4	H33A—C33—H33B	109.5
C15—C16—C11	118.5 (6)	C31—C33—H33C	109.5
C15—C16—H16	120.7	H33A—C33—H33C	109.5
C11—C16—H16	120.7	H33B—C33—H33C	109.5
C18—C17—C5	114.9 (5)	C35—C34—C30	112.1 (5)
C18—C17—H17A	108.5	C35—C34—H34A	109.2
C5—C17—H17A	108.5	C30—C34—H34A	109.2
C18—C17—H17B	108.5	C35—C34—H34B	109.2
C5—C17—H17B	108.5	C30—C34—H34B	109.2
H17A—C17—H17B	107.5	H34A—C34—H34B	107.9
C19—C18—C17	126.1 (6)	C36—C35—C34	129.7 (9)
C19—C18—H18	116.9	C36—C35—H35	115.2
C17—C18—H18	116.9	C34—C35—H35	115.2
C18—C19—C21	124.0 (6)	C35—C36—C38	125.0 (12)
C18—C19—C20	119.8 (6)	C35—C36—C37	119.9 (11)
C21—C19—C20	116.2 (6)	C38—C36—C37	115.0 (9)
C19—C20—H20A	109.5	C36—C37—H37A	109.5
C19—C20—H20B	109.5	C36—C37—H37B	109.5
H20A—C20—H20B	109.5	H37A—C37—H37B	109.5
C19—C20—H20C	109.5	C36—C37—H37C	109.5
H20A—C20—H20C	109.5	H37A—C37—H37C	109.5
H20B—C20—H20C	109.5	H37B—C37—H37C	109.5
C19—C21—H21A	109.5	C36—C38—H38A	109.5
C19—C21—H21B	109.5	C36—C38—H38B	109.5
H21A—C21—H21B	109.5	H38A—C38—H38B	109.5
C19—C21—H21C	109.5	C36—C38—H38C	109.5
H21A—C21—H21C	109.5	H38A—C38—H38C	109.5
H21B—C21—H21C	109.5	H38B—C38—H38C	109.5
C6—C22—H22A	109.5
C31—O2—C2—C3	−142.2 (4)	C17—C5—C9—C1	173.2 (4)
C31—O2—C2—C1	42.4 (6)	C4—C5—C9—C1	54.1 (5)
C9—C1—C2—O2	−157.5 (4)	C6—C5—C9—C1	−63.8 (5)
C29—C1—C2—O2	−35.2 (6)	C2—C3—C10—O4	−89.8 (6)
C8—C1—C2—O2	87.0 (5)	C4—C3—C10—O4	86.0 (6)
C9—C1—C2—C3	27.3 (6)	C2—C3—C10—C11	88.8 (6)
C29—C1—C2—C3	149.6 (5)	C4—C3—C10—C11	−95.3 (5)
C8—C1—C2—C3	−88.2 (6)	O4—C10—C11—C12	−177.7 (5)
O2—C2—C3—C4	−171.5 (4)	C3—C10—C11—C12	3.6 (7)
C1—C2—C3—C4	3.8 (7)	O4—C10—C11—C16	2.6 (8)
O2—C2—C3—C10	4.2 (6)	C3—C10—C11—C16	−176.0 (5)
C1—C2—C3—C10	179.5 (4)	C16—C11—C12—C13	0.7 (9)
C2—C3—C4—O3	174.5 (5)	C10—C11—C12—C13	−179.0 (5)
C10—C3—C4—O3	−1.4 (7)	C11—C12—C13—O5	179.7 (6)
C2—C3—C4—C5	−7.9 (6)	C11—C12—C13—C14	0.8 (10)
C10—C3—C4—C5	176.2 (4)	O5—C13—C14—C15	179.2 (7)
O3—C4—C5—C9	157.9 (4)	C12—C13—C14—C15	−2.0 (11)
C3—C4—C5—C9	−19.7 (6)	C13—C14—C15—C16	1.7 (12)
O3—C4—C5—C17	37.2 (6)	C14—C15—C16—C11	−0.3 (10)
C3—C4—C5—C17	−140.4 (4)	C12—C11—C16—C15	−0.9 (9)
O3—C4—C5—C6	−86.6 (6)	C10—C11—C16—C15	178.7 (5)
C3—C4—C5—C6	95.8 (5)	C9—C5—C17—C18	−65.5 (6)
C9—C5—C6—C23	179.1 (4)	C4—C5—C17—C18	53.4 (6)
C17—C5—C6—C23	−58.9 (6)	C6—C5—C17—C18	175.3 (5)
C4—C5—C6—C23	62.2 (5)	C5—C17—C18—C19	146.8 (6)
C9—C5—C6—C7	56.0 (5)	C17—C18—C19—C21	−2.5 (11)
C17—C5—C6—C7	178.0 (4)	C17—C18—C19—C20	179.4 (6)
C4—C5—C6—C7	−60.8 (5)	C8—C7—C24—C25	−127.5 (5)
C9—C5—C6—C22	−62.6 (6)	C6—C7—C24—C25	101.2 (6)
C17—C5—C6—C22	59.4 (6)	C7—C24—C25—C26	−132.7 (7)
C4—C5—C6—C22	−179.4 (4)	C24—C25—C26—C28	4.3 (11)
C23—C6—C7—C8	−174.4 (4)	C24—C25—C26—C27	−176.1 (7)
C22—C6—C7—C8	67.6 (5)	C9—C1—C29—C30	103.1 (5)
C5—C6—C7—C8	−50.8 (6)	C2—C1—C29—C30	−15.3 (6)
C23—C6—C7—C24	−42.8 (6)	C8—C1—C29—C30	−137.5 (5)
C22—C6—C7—C24	−160.8 (4)	C1—C29—C30—C31	59.5 (6)
C5—C6—C7—C24	80.8 (5)	C1—C29—C30—C34	−173.6 (5)
C6—C7—C8—C1	49.5 (6)	C2—O2—C31—C32	124.8 (5)
C24—C7—C8—C1	−84.1 (6)	C2—O2—C31—C30	4.5 (6)
C9—C1—C8—C7	−51.4 (6)	C2—O2—C31—C33	−118.6 (5)
C2—C1—C8—C7	63.8 (6)	C29—C30—C31—O2	−53.9 (5)
C29—C1—C8—C7	−174.3 (5)	C34—C30—C31—O2	−179.2 (5)
C2—C1—C9—O1	124.2 (5)	C29—C30—C31—C32	−167.0 (5)
C29—C1—C9—O1	3.7 (6)	C34—C30—C31—C32	67.7 (7)
C8—C1—C9—O1	−117.8 (5)	C29—C30—C31—C33	64.2 (6)
C2—C1—C9—C5	−57.3 (5)	C34—C30—C31—C33	−61.1 (7)
C29—C1—C9—C5	−177.8 (4)	C31—C30—C34—C35	−159.6 (6)
C8—C1—C9—C5	60.7 (5)	C29—C30—C34—C35	75.5 (7)
C17—C5—C9—O1	−8.3 (6)	C30—C34—C35—C36	−137.6 (9)
C4—C5—C9—O1	−127.4 (5)	C34—C35—C36—C38	3.4 (15)
C6—C5—C9—O1	114.7 (5)	C34—C35—C36—C37	−174.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1i	0.82	2.05	2.785 (6)	150

(I)	O5	H5	O1i	0.82	2.05	2.785 (6)	149.7
Isogarcinol*	O5	H5	O1ii	0.82	2.115	2.792	139.7
Isogarcinol*	O6	H6	O5ii	0.82	2.067	2.882	172.9

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1i	0.82	2.05	2.785 (6)	150

Symmetry code: (i) .